93981-51-2

Basic information

• Product Name: [3-(allyloxy)propyl]benzene
• Synonyms: [3-(allyloxy)propyl]benzene;[3-(2-Propenyloxy)propyl]benzene;3-Phenylpropylallyl ether;Allyl(3-phenylpropyl) ether;Allylhydrocinnamyl ether;Hydrocinnamylallyl ether
• CAS NO: 93981-51-2
• Molecular Formula: C₁₂H₁₆O
• Molecular Weight: 176.25484
• EINECS: 301-137-1
• Mol File: 93981-51-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 255.1°Cat760mmHg
• Flash Point: 111.5°C
• Appearance: /
• Density: 0.928g/cm³
• Vapor Pressure: 0.0266mmHg at 25°C
• Refractive Index: 1.5
• CAS DataBase Reference: [3-(allyloxy)propyl]benzene(CAS DataBase Reference)
• NIST Chemistry Reference: [3-(allyloxy)propyl]benzene(93981-51-2)
• EPA Substance Registry System: [3-(allyloxy)propyl]benzene(93981-51-2)

Safety Data

• Hazardous Substances Data: 93981-51-2(Hazardous Substances Data)

Usage

Description

[3-(allyloxy)propyl]benzene, also known as allylphenyl ether, is an organic compound characterized by its chemical formula C12H16O. It is a clear, colorless liquid with a faint sweet, floral odor. [3-(allyloxy)propyl]benzene is synthesized through the reaction of allyl chloride with phenol in the presence of a base, and it is recognized for its versatility in various applications across different industries.

Uses

Used in Perfumery and Flavor Industry:
[3-(allyloxy)propyl]benzene is used as a fragrance additive for its sweet, floral scent, making it a valuable component in the perfumery industry. It also contributes to the creation of flavoring agents, enhancing the sensory experience of various products.
Used in Pharmaceutical Production:
In the pharmaceutical industry, [3-(allyloxy)propyl]benzene serves as a key intermediate in the synthesis of various medicinal compounds. Its unique chemical structure allows for its incorporation into the development of new drugs and pharmaceutical products.
Used in Agricultural Products:
[3-(allyloxy)propyl]benzene is also utilized in the agricultural sector, where it plays a role in the production of certain agricultural products, potentially contributing to the efficiency and effectiveness of these items.
Used in Organic Synthesis:
As a versatile intermediate in organic synthesis, [3-(allyloxy)propyl]benzene is employed in the chemical industry for a wide range of applications. Its chemical structure makes it suitable for use in the development of new compounds and materials, further expanding its utility across various sectors.

InChI:InChI=1/C12H16O/c1-2-10-13-11-6-9-12-7-4-3-5-8-12/h2-5,7-8H,1,6,9-11H2

Upstream product

• 122-97-4 3-Phenyl-1-propanol 
• 107-05-1 3-chloroprop-1-ene 
• 35466-83-2 allyl methyl carbonate 
• 70122-89-3 tert-butyl allyl carbonate 
• 70122-88-2 allyl isopropyl carbonate 
• 104-53-0 3-phenyl-propionaldehyde 
• 18146-00-4 allyloxytrimethylsilane 
• 70770-06-8 1-benzyloxy-3-phenylpropane 
• 501-52-0 3-Phenylpropionic acid 
• 15814-45-6 allyl 3-phenylpropionate 
• 101-37-1 triallyl cyanurate 

Downstream Products

• 106-41-2 4-bromo-phenol 
• 122-97-4 3-Phenyl-1-propanol 
• 85909-41-7 3-phenylpropyl acrylate 
• 80910-19-6 2-<(3-phenylpropoxy)methyl>oxirane 

Relevant articles and documents

Study of O-allylation using triazine-based reagents

Acid-catalyzed allylating reagent 2,4,6-tris(allyloxy)-1,3,5-triazine (TriAT-allyl) and its substituted derivatives have been developed. The reaction of acid-, and alkali-labile alcohols with these reagents in the presence of a catalytic amount of trifluoromethanesulfonic acid (TfOH) afforded the corresponding allyl ethers in good yields. Reactions using these reagents with an unsymmetrically-substituted regioisometric allyl group suggested that a single isometric allylic cation species would be involved.

Oxidation of acyclic alkenes and allyl and benzyl ethers with DIB/t-BuOOH/Mg(OAc)2

Oxidation of (11Z)-1′,2′-didehydrostemofoline with DIB/TBHP/Mg(OAc)2·4H2O resulted in oxidative cleavage of the C-11-C-12 double bond instead of the desired allylic oxidation of the 1-butenyl side chain. Stemofoline gave a similar result. The oxidation of more simple terminal alkenes was regioselective and gave vinyl ketones while allyl and benzyl ethers gave acrylate and benzoate esters, respectively. Allyl and benzyl ethers could be chemoselectively oxidized in the presence of a terminal alkene or benzyl group. Oxidation of an internal alkene was poorly regioselective, in contrast to the oxidation of 1-substituted cyclohexenes.

General method for the palladium-catalyzed allylation of aliphatic alcohols

A palladium catalysis-mediated approach to coupling aliphatic alcohols with allyl carbonates has been developed. The method allows for the allylation of primary, secondary, and tertiary alcohols efficiently under mild conditions. Limitations were explored as well as the asymmetric application of the chemistry. Regiochemical and olefin geometry was controlled in the coupling of unsymmetrical allylating agents. Transient allyl carbonates were observed in the coupling, which comprised the trans-carboxylation of the allyl-carbonate with the requisite alcohol.